50 days in Vermont Itinerary

50 days in Vermont Itinerary

Created using Inspirock Vermont attractions planner

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Route & dates

50 days in Vermont Itinerary

Start: Toronto
+2
ferry + Fly + bus:  6​h 30​min
1
Burlington
— 11 nights
Drive:  1​h 30​min
2
Jay
— 9 nights
Drive:  1​h 15​min
3
Saint Johnsbury
— 10 nights
Drive:  1​h 30​min
4
Woodstock
— 10 nights
Drive:  1​h 45​min
5
Bennington
— 9 nights
Drive + Fly:  8​h 45​min
End: Toronto

11
nights
Burlington

Burlington ©
Burlington is the most populous city in the U.S. Attractions like ECHO, Leahy Center for Lake Champlain and Shelburne Bay Park make great kid-friendly stops. Get out of town with these interesting Burlington side-trips: Lake Champlain Maritime Museum (in Vergennes), Stowe (The Alchemist, Stowe Recreation Path, & more) and Waterbury Center (Cabot Farmers' Store & GreenSpark Sustainability Park). There's much more to do: get a taste of the local shopping with Church Street Marketplace, savor the flavors at Food & Drink, indulge your thirst for a good beer at Switchback Brewing, and contemplate the long history of Ethan Allen Homestead.

To find traveler tips, maps, other places to visit, and more tourist information, read our Burlington online holiday planner .

Toronto, Canada to Burlington is an approximately 6.5-hour combination of ferry, flight, and bus. You can also do a combination of flight and bus; or drive. In July, daily temperatures in Burlington can reach 32°C, while at night they dip to 19°C. Finish up your sightseeing early on the 15th (Wed) so you can go by car to Jay.

Things to do in Burlington

Parks Outdoors Nature

Side Trips

Stowe, Shelburne, Montpelier, Waterbury Center, Magic Hat Brewing Company
Highlights from your plan
Church Street Marketplace ©
Church Street Marketplace
ECHO, Leahy Center for Lake Champlain ©
Smugglers' Notch Resort ©
Smugglers' Notch Resort

9
nights
Jay

Jay ©
Jay is one of the northernmost towns in Orleans County, Vermont, United States, located on the Canada–US border. Attractions like Jay Peak Pump House and Jay Peak Resort make great kid-friendly stops. Explore the numerous day-trip ideas around Jay: Newport Bike Path (in Newport), Jed's Maple Products (in Derby) and Grand Isle State Park (in Grand Isle). There's still lots to do: explore the activities along Lake Memphremagog, indulge your thirst for a good beer at Rock Art Brewery, don't miss a visit to Cold Hollow Sculpture Park, and take an in-depth tour of Old Stone House Museum.

Before you visit Jay, use our trip planner to discover what you can do and see there.

You can drive from Burlington to Jay in 1.5 hours. Expect slightly colder temperatures when traveling from Burlington in July; daily highs in Jay reach 28°C and lows reach 15°C. You will leave for Saint Johnsbury on the 24th (Fri).

Things to do in Jay

Parks Nature Outdoors

Side Trips

Newport, Montgomery, Hyde Park, Rock Art Brewery, Kingdom Brewing
Highlights from your plan
Jay Peak Resort ©
Jay Peak Resort
Lake Memphremagog ©
Lake Memphremagog
Grand Isle State Park ©
Grand Isle State Park

10
nights
Saint Johnsbury

Saint Johnsbury ©
St. Family-friendly places like Great Vermont Corn Maze and Vermont Granite Museum will thrill your kids. Explore the numerous day-trip ideas around Saint Johnsbury: Bragg Farm Sugar House & Gift Shop (in Montpelier), Sunset Lake Floating Bridge (in Brookfield) and Martin Bridge Park (in Marshfield). And it doesn't end there: walk around Dog Mountain Home of Stephen Huneck Gallery, explore the activities along Lake Willoughby, stroll through Lamoille Valley Rail Trail, and get to know the fascinating history of The Long Trail.

To find other places to visit, ratings, photos, and more tourist information, refer to the Saint Johnsbury trip maker .

Traveling by car from Jay to Saint Johnsbury takes 1.5 hours. In July, daytime highs in Saint Johnsbury are 30°C, while nighttime lows are 17°C. Finish up your sightseeing early on the 3rd (Mon) so you can go by car to Woodstock.

Things to do in Saint Johnsbury

Parks Nature Museums

Side Trips

Groton, Vermont, Barre, Glover, East Burke
Highlights from your plan
Great Vermont Corn Maze ©
Great Vermont Corn Maze
Museum of Everyday Life ©
Museum of Everyday Life

10
nights
Woodstock

Woodstock ©
Woodstock is the shire town of Windsor County, Vermont, United States. Kids will appreciate attractions like Montshire Museum of Science and Okemo Mountain Resort. Change things up with these side-trips from Woodstock: Rutland (Rutland murals & Wonderfeet Kids Museum), Pond Hill Ranch (in Castleton) and Killington (Killington Resort & Killington - Pico Adventure Center). There's lots more to do: experience rural life at Sugarbush Farm, identify plant and animal life at Vermont Institute of Natural Science (VINS) Nature Center, soar above the sights with a balloon tour, and contemplate the long history of Marsh - Billings - Rockefeller National Historical Park.

To see ratings, maps, where to stay, and tourist information, read our Woodstock trip planner .

Traveling by car from Saint Johnsbury to Woodstock takes 1.5 hours. In August, plan for daily highs up to 32°C, and evening lows to 15°C. Finish your sightseeing early on the 13th (Thu) to allow enough time to drive to Bennington.

Things to do in Woodstock

Parks Outdoors Historic Sites

Side Trips

Quechee, Brandon, Killington, Ludlow, Rutland
Highlights from your plan
Montshire Museum of Science ©
Montshire Museum of Science
Okemo Mountain Resort ©
Okemo Mountain Resort
Upper Valley Aquatic Center ©
Upper Valley Aquatic Center

9
nights
Bennington

Bennington ©
Bennington is a town in Bennington County, Vermont, in the United States. Attractions like Bromley Mountain and Adams Farm make great kid-friendly stops. Venture out of the city with trips to Vermont Country Store (in Weston), Brattleboro (Creamery Covered Bridge & Saxtons Distillery) and Manchester (Equinox Preservation Trust, Dana L. Thompson Memorial Park, & more). There's still lots to do: get great views at Bennington Battle Monument, relax in the rural setting at Mad Tom Orchard, take in the awesome beauty at Equinox Mountain, and stroll the grounds of New Catholic Cemetery.

For where to stay, ratings, reviews, and other tourist information, go to the Bennington online trip itinerary planner .

Traveling by car from Woodstock to Bennington takes 2 hours. In August, daytime highs in Bennington are 30°C, while nighttime lows are 15°C. Wrap up your sightseeing by early afternoon on the 22nd (Sat) to allow time for travel back home.

Things to do in Bennington

Parks Nature Winter Sports

Side Trips

Manchester, Wilmington, Putney, Brattleboro, Arlington
Highlights from your plan
Hildene, The Lincoln Family Home ©
Hildene, The Lincoln Family Home
Bromley Mountain ©
Bromley Mountain
Lye Brook Falls ©
Lye Brook Falls

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